Travel Guide: Chicago (Part Duex)

While Joanna explored the Windy City a year before me - we were lucky enough to check out different parts of the city. I had 2.5 days to explore and ended up walking over 27 miles. (Needless to say we saw it all)

THURSDAY NIGHT:

Our first stop (after a 13 hour car ride) food. We heard about Big Star TacoOn a Thursday night there was still quite a wait so I'd make a reservation, or if you're in a hurry they have a take out window that has limited options and a few alcoholic beverages. But if you want the full menu definitely wait it out.

May I suggest the fish tacos and of course the margaritas.

After dinner we headed across the street to a popular speak easy The Violet Hour (because yes Chicago has speakeasy's)

The door changes periodically but it usually appears as an art installation. There are no photos allowed and cell phones are prohibited, but there's an absinthe happy hour - so be prepared.

FRIDAY:

We started early and headed downtown in search of coffee and breakfast. I cannot say nicer things about Goddess and the Baker. This place has a pastry case packed to the brim, outside seating (which I thought was impossible in Downtown Chicago), lots of room, delicious food, and amazing coffee.

I was happy to take a little site seeing break and stop at this place. (Also for some reason Chicago has a thing for "signs" in resturants so get ready for a lot of those).

From breakfast it was just a short walk to the "The Loop" - Chicago's largest downtown area. There are tons of skyscrapers and provide some great photo op's but besides that there isn't a ton to do here. I suggest walking past on your way to "The Bean" at Millennium Park

Cloud Gate - as it's known - is where the silver bean is housed in Chicago's Downtown district. Usually littered with tourist this is again something to grab a quick photo with and be on your way.

It was a steamy summer day in the Windy City which allowed us to stop for multiple coffee breaks (also I was still nursing my newly healed broken leg at the time.) Luckily we stumbled upon Intelligentsia Coffee This was some of the best coffee I had ever tasted and smelled (we even brought a few bags home with us)

Did you know Chicago has beaches? Well really it's like some sand surrounding a lake but it was PACKED the day we were there. We happened to stumble upon the annual Air & Water show. Where jets fly all throughout the city over the water making jet stream patterns. It was quite fun but definitely put a damper on my beach going experience. Did put my feet in the water though.

And since it was on the way back to our car we walked through the Botanical Gardens.

We ended our journey at Brightwok - an affordable and filling asian resturants. You get to build your own bowl with either rice or noodles and then load up with 4 veggies and a meat.

Definitely a great way to end our first real day in the city.

SATURDAY:

We woke up early to hit the South Side of Chicago - and grabbed breakfast at an amazing coffee shop called Robust - I ordered the oreo waffles and Andrew snagged the banana foster.

Then we hit up the more hipster neighborhoods, got to walk through a Spanish food festival, and took some photos in front of some amazing street art that litter's the city.

(For a guide on the best Chicago murals - check out this post)

Next we hit up the Milwaukee Ave area of Chicago - home to great food - amazing houses - scenic views and of course The Wormhole - an 80's themed cafe that even has it's own Delorean. Fun fact they even served Videri Chocolate !

I can't go to a new city without stopping by a record store and searching for a copy of New Order's - Power, Corruption, & Lies (an old copy not a remastered one) And while I didn't find it at Reckless Records I did walk away with quite a few new ones for my table.

And for a city that boasts about deep dish pizza and pickles on their hot dogs we didn't eat any of those things during our stay. Instead we had a ton of Asian food.

En Hakkore's specialty is their poke bowls. Yum! Also if you want to split a dish their korean beef fries are killer.

With only a few more hours to spend in Chicago and a desperate need to find the "Chicago" Mural - we trekked over the Milwaukee Ave bridge to the other side of town and hit up a crazy VHS rental place that was something out of High Fidelity (if they collected movies instead of records) called Odd Obsession.

Just walking through there can kill some time and find some movies you've never heard of.

Finally we made it to the mural after 3 miles of walking (yes everyone hated me) but we got to see parts of the city that we wouldn't have otherwise and stumbled upon another cool record store that I don't have photos of (but if you're desperate to see this mural I'd suggest calling an Uber or renting a bicycle)

So that was my 52 hours in Chicago. We walked over 27 miles and saw a ton of stuff - even though I consider the trip pretty leisurely when it comes to how much I normally accomplish on a "trip"

If you're looking for more Chicago reccomendations check out our Chicago Part 1 blog here.